The once plentiful petroleum reserves, which have served as the principal source of cheap, ubiquitous antecedents to most commodity chemicals for decades, are projected to peak over the next few years. Once achieved, the years following will manifest circumstances where supply is outstripped by demand, a corollary of which is a steady, unchecked price escalations of foods and other consumables. Thus, it is incumbent for scientists around the world to search for more sustainable surrogates, particularly those derived from biomass. A subdivision of biomass is a genre of diverse, panoptic materials termed carbohydrates or sugars (i.e., hexoses and pentoses), that can readily be transformed into polytropic derivatives.
One such derivative, readily made from the regioselective dehydroxylation of sorbitol, a C6 sugar alcohol that is produced on the industrial scale primarily from the reduction of glucose, is 1,2,5,6-hexanetetrol.
1,2,5,6-hexanetetrol (HTO) is a rare, tetrafunctional substrate, auspicious as a precursor to copious derivatives that, owing to their agricultural production, can be deemed as “green” or “renewable”. The intrinsic, multiple sites of chirality is a feature of particular appeal to the medicinal chemist, as the vast majority of pharmaceuticals contain one or more stereocenters. By virtue of the prodigious quantities isolated from corn and other plant materials, sorbitol provides an enticing platform on which to perform such modifications, and furthermore permits the realization of useful derivatives economically.
The multiple alcohol moieties inherent in HTO can serve as nucleophiles in some aspects, and as sites for further functionalization in others. The present disclosure describes several derivatives of HTO useful as building blocks for further compounds, including amphiphilic compounds that are useful in a variety of applications.